WO1997035842A1 - Compositions cosmetiques a base de pyrazolin-4,5-diones, nouvelles pyrazolin-4,5-diones, procedes de preparation et utilisations - Google Patents

Compositions cosmetiques a base de pyrazolin-4,5-diones, nouvelles pyrazolin-4,5-diones, procedes de preparation et utilisations Download PDF

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Publication number
WO1997035842A1
WO1997035842A1 PCT/FR1997/000438 FR9700438W WO9735842A1 WO 1997035842 A1 WO1997035842 A1 WO 1997035842A1 FR 9700438 W FR9700438 W FR 9700438W WO 9735842 A1 WO9735842 A1 WO 9735842A1
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WO
WIPO (PCT)
Prior art keywords
radical
pyrazolin
dione
methyl
phenyl
Prior art date
Application number
PCT/FR1997/000438
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English (en)
French (fr)
Inventor
Gérard Malle
Laurent Vidal
Original Assignee
L'oreal
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by L'oreal filed Critical L'oreal
Priority to EP97914378A priority Critical patent/EP0888306B1/de
Priority to JP53406797A priority patent/JP3327925B2/ja
Priority to US09/155,213 priority patent/US6322775B1/en
Priority to DE69705825T priority patent/DE69705825T2/de
Priority to AU21644/97A priority patent/AU2164497A/en
Priority to AT97914378T priority patent/ATE203520T1/de
Publication of WO1997035842A1 publication Critical patent/WO1997035842A1/fr
Priority to US09/964,605 priority patent/US20020031536A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/28—Two oxygen or sulfur atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/04—Preparations for care of the skin for chemically tanning the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes

Definitions

  • the present invention relates to new cosmetic compositions, in particular for coloring the skin and / or the hair, comprising, in a cosmetically acceptable carrier, at least one pyrazolin-4,5-dione.
  • the invention also relates to new pyrazolin-4,5-diones, to their methods of preparation and to their uses in the cosmetic field, in particular for coloring the skin and more particularly with a view to giving the latter a tanning appearance. .
  • DHA dihydroxyacetone
  • DHA is a particularly interesting product which is commonly used in cosmetics as an artificial tanning agent for the skin; applied on the latter, in particular on the face, it makes it possible to obtain a tanning or browning effect of appearance very close to that which can result from a prolonged exposure to the sun (natural tanning) or under a UV lamp.
  • Such use also has the advantage of completely avoiding the risks of skin reaction generally associated with the aforementioned prolonged exposures (erythema, burns, loss of elasticity, appearance of wrinkles, premature aging of the skin, and the like).
  • the intensity of the coloration obtained on the skin and especially the speed with which this coloration develops are often judged to be very insufficient by the users of self-tanning products based on DHA.
  • the duration necessary for the appearance on the skin of the desired intensity is generally several hours.
  • EP-A-547864 proposes to provide DHA in the presence of an amino acid and a silicone, the DHA and the amino acid being stored before application to the skin in different compartments.
  • application WO-A-9404130 which describes a device for supplying DHA at the same time as a primary amine, these two compounds also being stored in different compartments.
  • compositions are now proposed containing, in a cosmetically acceptable carrier, at least one pyrazolin-4,5-dione.
  • the time required to reveal the color after applying these compositions to the skin is remarkably short.
  • These compositions also have excellent stability and give the skin a color very close to that imparted by a natural tan. Finally, the resistance over time of the coloring on the skin is also remarkable.
  • compositions can find an interesting application in hair coloring.
  • the first object of the invention is therefore a new composition
  • a cosmetically acceptable carrier at least one pyrazolin-4,5 dione corresponding to formula (I) below:
  • R is chosen from - a hydrogen atom; a linear or branched C r C 18 alkyl radical optionally substituted by a hydroxyl (OH), sulfonyl (SO 3 H), carboxyl (COOH) or hydroxyalkyl C 2 -C 4 radical; a cyclohexyl or cyclopentyl radical;
  • n 1, 2 or 3
  • X is a hydrogen atom or a methyl radical
  • Y is a methyl, hydroxy or C 1 -C 5 alkoxy radical , linear or branched;
  • R' represents a phenyl or naphthyl radical substituted or not and p is equal to 1 or 2;
  • phenyl radical substituted or not by a maximum of 2 radicals chosen from methyl, trifluoromethyl, methoxy or sulfonyl radicals;
  • - a phenyl radical a phenyl radical substituted by a nitro radical; a phenyl radical substituted by one to three radicals chosen from: -COOH, -CH 2 COOH, -Cl, -Br, -F, -OH, -SO 3 H, -CH 2 OH, -OCF 3l -CF
  • -SO 2 NH 2 , -SO 2 NHC 2 H 5 , - SO 2 NHCH 2 CH 2 OH, -CON (CH 3 ) 2 , -CON (C 2 H 5 ) 2 , -CH 2 N ( CH 3 ) 2 , -CH 2 N (C 2 H 5 ) 2 , -NHCOCH 3 , -NHCOC 2 H 5 , a C 1 -C 8 alkyl radical or -ZR 3 in which Z is an oxygen atom or of sulfur and R 3 is a hydrogen atom or a linear or branched C 1
  • benzyl radical a benzyl radical substituted with a radical -COOH, -OCH 3 or -SO 3 H;
  • a pyridyl radical a pyrimidinyl radical, a pyrazinyl radical, a triazinyl radical, a benzotriazolyl radical, a benzimidazolyl radical, a thienyl radical, an imidazolyl radical, a thiazolyl radical, a triazolyl-1,2,4 radical, an indazolyl radical , an indolyl radical, a quinolyl radical or an isoquinolyl radical;
  • R 2 is chosen from: - a hydrogen atom; a linear or branched C r C 6 alkyl radical; a C r C 4 hydroxyalkyl radical; a methoxymethyl radical;
  • a phenyl radical a phenyl radical substituted by a halogen atom, a nitro radical or a trifluoromethyl radical; a phenyl radical substituted by up to three radicals selected from alkyl C r -C 4 alkoxy, C, - C 4 dialkylamino, C r -C 4 alkylthio or C r C 2;
  • benzyl radical substituted by a halogen atom, a C 1 -C 4 alkyl radical, a C 1 -C 4 alkoxy radical, a trifluoromethyl radical or a C 1 -C 4 dialkylamino radical;
  • thienyl radical a furyl radical, a pyridyl radical or a pyrazolyl radical.
  • these compositions are intended for artificial tanning of the skin.
  • These new compositions have the advantage of giving the skin a tan very close to the natural tan, in an extremely short time. Indeed, a few minutes are enough to obtain a tanned complexion.
  • Another subject of the present invention is a method of cosmetic treatment of the skin intended for tanning and / or artificially browning it, consisting in applying to it an effective amount of a cosmetic composition in accordance with the invention or of a pyrazolin-4,5-dione as mentioned above.
  • the present invention also relates to the use of a pyrazolin-4,5-dione as mentioned above in, or for the manufacture of, compositions intended for artificial tanning and / or browning of the skin.
  • these cosmetic compositions are intended for coloring the hair.
  • the present invention thus also relates to a method of cosmetic treatment of the hair intended to color them, consisting in applying to the hair an effective amount of a composition in accordance with the invention or of a pyrazolin-4,5-dione such than mentioned above.
  • the present invention also relates to the use of a pyrazolin-4,5-dione as mentioned above in, or for the manufacture of, compositions intended for coloring the hair.
  • R is chosen from: - a hydrogen atom; a linear or branched C1-C8 alkyl radical,
  • a phenyl radical optionally substituted by a nitro radical, a -Cl radical, a C1-C4 alkyl radical or a C1-C4 alkoxy radical,
  • R 2 is chosen from:
  • phenyl radical optionally substituted by a halogen atom, a nitro radical, a C1-C4 alkyl radical or a C1-C4 alkoxy radical;
  • pyrazolin-4,5-diones which can be used in the compositions in accordance with the invention, there may be mentioned in particular: - 3-methyl 1-phenyl pyrazol ⁇ n-4,5-d ⁇ one, 1-phenyl pyrazol ⁇ n-4,5-d ⁇ one, 3- tert-butyl 1-phenyl pyrazol ⁇ n-4,5-dione, 1, 3- d ⁇ phenyl pyrazol ⁇ n-4,5-d ⁇ one, 1- phenyl 3- (4'-methylphenyl) pyrazol ⁇ n-4,5-d ⁇ one; 1-phenyl 3- (3'-methoxymethyl) pyrazol ⁇ n-4,5-d ⁇ one, 1-phenyi 3- (4'-methoxyphenyl) pyrazolin -4,5-d ⁇ one, 1- 1- dozens ⁇ yl 3- (4'- n ⁇ trophenyl) pyrazol ⁇ n-4,5-d ⁇ one; lavS-methoxy 1-phenyl pyrazolin-4,5-d
  • pyrazolin-4,5-diones which can be used in the context of the present invention, very particularly preferred are those for which, cumulatively, R, is chosen from:
  • R 2 is chosen from:
  • compositions according to the invention it is more particularly preferred to use 3-methyl 1-phenyl pyrazolin-4,5-dione; 3-methyl pyrazolin ⁇ 4,5-dione; 1,3-dimethyl pyrazolin-4,5-dione; 1-ethyl 3-methyl pyrazolin-4,5-dione; 1- isopropyl 3-methyl pyrazolin-4,5-dione; ia 1-tertbutyl 3-methyl pyrazolin-4,5-dione; 1-methyl 3-phenyl pyrazolin-4,5-dione; 1-methyl 3- (3'-methoxyphé ⁇ yl) pyrazolin-4,5-dione; 3 (2'-furyl) 1-methyl pyrazolin-4,5-dione; 1-methyl 3- (4'-pyridyl) pyrazolin-4,5-dione; 1-methyl 3-methoxy pyrazoiin-4,5-dione; 3-ethoxy 1-methyl pyrazolin-4,5-d
  • the pyrazolin-4,5-diones are used in an amount effective to impart coloring either to the skin or to the hair, as the case may be. Thus, they are generally present in the compositions according to the invention at a concentration of between 0.05 and 10% by weight, preferably between 0.05 and 5% by weight, relative to the total weight of the composition.
  • the pH can vary between 3 and 10. It is preferably between 3 and 7.
  • the pH can vary between 2 and 8. It is preferably between 2 and 6.
  • the vehicle (or cosmetically acceptable support) for the compositions according to the invention is preferably water, alone or with one or more organic solvents or fatty substances.
  • the solvents which can be used are preferably chosen from alcohols such as ethyl alcohol or cetyl alcohol, or also from propylene glycol, ethylene glycol monoethyl ether and ethylene glycol monobutyl ether.
  • oils and waxes of mineral, animal or vegetable origin there may be mentioned oils and waxes of mineral, animal or vegetable origin.
  • oil By oil is meant a compound which is liquid at room temperature.
  • the term “wax” is intended to mean a compound which is solid or substantially solid at room temperature, and the melting point of which is generally greater than 35 ° C.
  • oils mention may be made of mineral oils (petrolatum); vegetable (sweet almond, macadamia, blackcurrant seed oil); synthetics such as perhydrosqualene, alcohols, fatty acids or esters (octyl palmitate, isopropyl lanolate, triglycerides including those of capric / caprylic acids), fatty esters and ethers oxyethylenated or oxypropylenated; silico ⁇ ées (cyclométhico ⁇ e, polydiméthysiioxanes ou PDMS) or fluorinated, polyalkylenes.
  • mineral oils petrolatum
  • vegetable sweet almond, macadamia, blackcurrant seed oil
  • synthetics such as perhydrosqualene, alcohols, fatty acids or esters (octyl palmitate, isopropyl lanolate, triglycerides including those of capric / caprylic acids), fatty esters and ethers oxye
  • waxy compounds mention may be made of jojoba oil, paraffin, carnauba wax, beeswax, hydrogenated castor oil.
  • compositions targeted by the invention in particular thickeners, emulsifiers, gelling agents are those which are conventionally used in the cosmetic and / or dermatological field.
  • poiyalkoxylated fatty alcohols are used such as oxypropylene butyl alcohols, oxyethylenated caprylic alcohols, oxyethylenated cetyl alcohols.
  • thickeners it is possible to use crosslinked polyacrylic acids, guar gums and modified or unmodified celluloses such as hydroxypropylated guar gum, methylhydroxyethylcellulose, hydroxypropylmethyl cellulose or also hydroxyethylceilulose.
  • gelling agents mention may be made of modified clays (bentones), metal salts of fatty acids (aluminum stearate), ethylene / acrylate copolymers, silicas, polyethylenes, calcium silicates or ethylcellulose.
  • compositions according to the invention may also contain any other cosmetically or dermatologically acceptable constituent usually used in this type of composition, such as softeners, antioxidants, opacifiers, stabilizers, emollients, repellents against insects, organic sunscreens active in UV-A and / or UV-B, photoprotective pigments and nanopigments, hydrating agents, vitamins, perfumes, preservatives, fillers, sequestrants, dyes, and in particular the compounds known for their self-tanning action such as, for example, dihydroxyacetone, methylglycoxal, glyceric aldehyde, erythrulose, alloxan, 2,3-dihydroxysuccinic dialdehyde, 2-amino-3-hydroxysuccinic dialdehyde , 2-benzylamino-3-hydroxysuccinic dialdehyde.
  • any other cosmetically or dermatologically acceptable constituent usually used in this type of composition such as softeners, antioxidants, opacifiers, stabilizer
  • This composition may be in particular in the form of a simple or complex emulsion (O / W, W / O, O / W / O or W / O / W) such as a cream, a milk, a gel or a cream gel, powder, solid stick and optionally be packaged as an aerosol and be in the form of a foam or spray.
  • a simple or complex emulsion O / W, W / O, O / W / O or W / O / W
  • a cream, a milk, a gel or a cream gel, powder, solid stick such as a cream, a milk, a gel or a cream gel, powder, solid stick and optionally be packaged as an aerosol and be in the form of a foam or spray.
  • this composition is in the form of an oil-in-water emulsion
  • compositions concerned by the invention can be prepared according to techniques well known to those skilled in the art, in particular those intended for the preparation of emulsions of the oil-in-water or water-in-oil type.
  • the present invention also relates to new pyrazol ⁇ n-4,5-d ⁇ ones corresponding to the following general formula (! '):
  • R ⁇ and R ' 2 have the same meanings as those indicated above for R, and R 2 in formula (I) with the following reservations:
  • R ′ 2 is different from a hydrogen atom, a methyl radical, a tert-butyl radical, a radical phenyl, a p-methylphenyl radical, a p-nitrophenyl radical or a p-methoxyphenyl radical,
  • R ′ 2 represents a methyl radical
  • R ′ is different from a p-nitrophenyl radical, from a 2-phenoxyethyl radical, from a 2-naphthyloxyethyl radical, from a methyl radical, from an m-trifluoromethylbenzyl radical, a 1- phenylethyl radical, a p-methylphenyl radical, a 1-cyclohexylethyl radical or a 1- (3 ', 4'-dichlorophenyl) ethyl radical,
  • R ' when R 'represents a 2-naphthyloxyethyl radical, R' 2 is different from an n-propyl radical or a hydroxymethyl radical,
  • R ′ represents a 2-phenoxy-ethyl radical
  • R ′ 2 is different from a tert-butyl radical
  • R ' 2 represents a methoxymethyl radical
  • R' is different from a 2-naphthyloxyethyl radical or from a 1- (3 ', 4'-dichlorophenyl) ethyl radical
  • R ′ represents a hydrogen atom
  • R ′ 2 is different from a methyl radical
  • R ' 2 represents a phenyl radical
  • R' is different from a methyl radical, a p-methoxyphenyl radical or a p-nitrophenyl radical.
  • R ′ is chosen from:
  • a phenyl radical optionally substituted by a nitro radical, a -Cl radical, a C1-C4 alkyl radical or a C1-C4 alkoxy radical,
  • R ' 2 is chosen from:
  • phenyl radical optionally substituted by a halogen atom, a nitro radical, a C1-C4 alkyl radical or a C1-C4 alkoxy radical;
  • R 2 ' chosen from:
  • the invention also relates to a first process for the preparation of the new compounds of formula (I '), this process being characterized in that it comprises the following steps (the meanings of R'-j and R'2 are such as given above):
  • this reaction being preferably carried out in a lower alcohol such as methanol, ethanol or isopropanol at a temperature between 65 ° C and 85 "C, at reflux of the solvent used, and preferably in the presence of a base low carbonate or bicarbonate type in catalytic amount,
  • a lower alcohol such as methanol, ethanol or isopropanol
  • a base low carbonate or bicarbonate type in catalytic amount
  • the aromatic nitroso derivative of the first step is preferably a p-nitrosodialkylaniiine of formula ⁇ ':
  • R 5 and R 6 represent a linear or branched C 4 -C 4 alkyl radical.
  • the acid hydrolysis of the second step of the preparation process according to the invention is preferably carried out with dilute sulfuric acid or aqueous hydrochloric acid at room temperature in the presence of a co-solvent of ta pyrazolin-4 , 5-dione, immiscible with water, which advantageously extracts the compound as it is formed, facilitating its isolation with very high purity.
  • the water-immiscible co-solvent can be a halogenated solvent such as, for example, dichloromethane or 1,2-dichloroethane.
  • the water-immiscible co-solvent is an ether such as diethyl or diisopropyl ether.
  • the subject of the invention is also a second process for the preparation of the new compounds of formula (I '), this process being characterized in that it comprises the following stages (the meanings of R'-
  • the first dibromination step is preferably carried out in an aqueous medium in the presence of 2 equivalents of bromine at room temperature.
  • the reaction is generally complete in a few hours: the dibromo derivative precipitates as it is formed, which allows isolation by simple filtration with high purity.
  • the second step is advantageously carried out at reflux of the acetic acid in a few hours, the lead dibromide which forms being able to be separated very easily by simple filtration.
  • the excipient is a water / ethanol / 1,2-propane diol mixture in a 1/2/1 weight ratio.
  • the colorings obtained with the formulas described above were evaluated by means of an in vivo test on three volunteers according to the following method: the formulas A, B and C were applied to the skin on 2.5 ⁇ 2.5 cm areas. delimited on the forearms of the three models. Then the intensity of coloring which was attached to each of the formulas was then determined after a certain time T, ie ⁇ L T. To do this, colorimetric measurements were carried out using a Minolta CM 1000 colorimeter. A first measurement was carried out just before the application of the products (To), a second 30 minutes after the application of the products ( T30min) > and a last 5 hours after applying the products (T5H).
  • composition A containing the 3-methyl-1-phenyl-2-pyrazolin-4,5-dione according to the invention leads to a skin coloration of faster appearance and greater intensity than the compositions B and C containing the DHA (with an equal content for B or 5 times higher for C than that of 3-methyl-1-phenyl-2-pyrazolin-4,5-dione).
  • phase A was brought to 80 ° C. separately. Then phase A was poured into phase B with Moritz stirring. The mixture was then homogenized and then allowed to cool to room temperature.
  • compositions in accordance with the invention for coloring the hair are given here of compositions in accordance with the invention for coloring the hair:
  • the pH of the composition was adjusted to 2.6 with 10% hydrochloric acid
  • This composition was applied for 30 minutes on locks of natural g ⁇ s hair containing 90% white and on locks of permanent g ⁇ s hair containing 90% white, at a rate of 2 to 5 g / g of hair.
  • the composition was applied either at room temperature (20 ° C) or at 50 ° C
  • the locks were then rinsed, either abundantly with tap water, or using a standard shampoo. They were then dried for 10 minutes, either with a hair dryer or under a helmet at a temperature between 60 and 65 ° C. The intensity of coloring of the locks was then determined.
  • L represents the luminance
  • Composition 2 is a composition of Composition 2:
  • the pH of the composition was adjusted to 5.8 with triethanolamine.
  • composition was applied 30 minutes to locks of hair of the same kind as above (natural gray hair at 90% white and to permanent gray locks at 90% white), at a rate of 2 to 5 g / g at a temperature of 37 ° C.
  • the locks were then rinsed and dried as above.
  • the intensity of their coloring was also measured as above.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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  • Plural Heterocyclic Compounds (AREA)
PCT/FR1997/000438 1996-03-22 1997-03-12 Compositions cosmetiques a base de pyrazolin-4,5-diones, nouvelles pyrazolin-4,5-diones, procedes de preparation et utilisations WO1997035842A1 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
EP97914378A EP0888306B1 (de) 1996-03-22 1997-03-12 Kosmetische zusammensetzungen auf der basis von pyrazolin-4,5-dionen,neue pyrazolin-4,5-dionen,verfahren zu ihrer herstellung und ihrer verwendung
JP53406797A JP3327925B2 (ja) 1996-03-22 1997-03-12 ４，５―ピラゾリンジオンを主成分とする化粧品組成物、新規な４，５―ピラゾリンジオン、その調製方法及びその使用
US09/155,213 US6322775B1 (en) 1996-03-22 1997-03-12 Cosmetic compositions containing pyrazolin-4,5-diones, novel pyrazolin-4,5-diones, preparation methods therefor and uses thereof
DE69705825T DE69705825T2 (de) 1996-03-22 1997-03-12 Kosmetische zusammensetzungen auf der basis von pyrazolin-4,5-dionen,neue pyrazolin-4,5-dionen,verfahren zu ihrer herstellung und ihrer verwendung
AU21644/97A AU2164497A (en) 1996-03-22 1997-03-12 Cosmetic compositions containing pyrazolin-4,5-diones, novel pyrazolin-4,5-diones, preparation methods therefor and uses thereof
AT97914378T ATE203520T1 (de) 1996-03-22 1997-03-12 Kosmetische zusammensetzungen auf der basis von pyrazolin-4,5-dionen,neue pyrazolin-4,5-dionen, verfahren zu ihrer herstellung und ihrer verwendung
US09/964,605 US20020031536A1 (en) 1996-03-22 2001-09-28 Cosmetic compositions based on 4,5-pyrazolinediones, novel 4,5-pyrazolinediones, process for their preparation and uses thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR96/03625 1996-03-22
FR9603625A FR2746391B1 (fr) 1996-03-22 1996-03-22 Compositions cosmetiques a base de pyrazolin-4,5-diones, nouvelles pyrazolin-4,5 diones, procedes de preparation et utilisations

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WO1997035842A1 true WO1997035842A1 (fr) 1997-10-02

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US (2) US6322775B1 (de)
EP (1) EP0888306B1 (de)
JP (1) JP3327925B2 (de)
AT (1) ATE203520T1 (de)
AU (1) AU2164497A (de)
CA (1) CA2249472A1 (de)
DE (1) DE69705825T2 (de)
ES (1) ES2162268T3 (de)
FR (1) FR2746391B1 (de)
WO (1) WO1997035842A1 (de)

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EP0873745A2 (de) * 1997-04-24 1998-10-28 Henkel Kommanditgesellschaft auf Aktien Mittel zum Färben von keratinhaltigen Fasern
WO1998051268A1 (fr) * 1997-05-13 1998-11-19 L'oreal Composition de teinture des fibres keratiniques comprenant une pyrazolin-4,5-dione et une amine primaire aromatique
US6537528B2 (en) 2000-07-12 2003-03-25 L'oreal S.A. Composition comprising at least one self-tanning agent chosen from monocarbonyl and polycarbonyl compounds and a flavylium salt compound which is unsubstituted in position 3, for coloring the skin, and uses thereof
EP1348424A1 (de) * 2002-03-28 2003-10-01 L'oreal Selbsbräunende Zusammensetzung ein Tetrahydrocurcuminoid und ein selbstbräunendes Mittel enthaltend
US6740313B2 (en) 2001-10-16 2004-05-25 L'oreal S.A. Compositions for giving the skin a coloration similar to that of a natural tan, based on a pigment of the monascus type, and uses thereof
US6875426B2 (en) 2002-03-28 2005-04-05 L'oreal Self-tanning composition containing a tetrahydrocurcuminoid and a self-tanning agent
EP1671680A1 (de) 2004-12-20 2006-06-21 L'oreal Selbstbräunerkombination, Mehrkammernvorrichtung und Verfahren zum Färben der Haut
EP1754513A2 (de) 2005-08-17 2007-02-21 L'oreal Verwendung von 8-Hexadecen-1,16-dicarbonsäure als Pflegemittel zur förderung der Hornschicht Kohäsion
EP2011481A2 (de) 2007-07-06 2009-01-07 L'Oreal Sonnenschutzzusammensetzung, die eine Verbindung aus einem halbkristallinen Polymer und hohle Latexpartikeln enthält
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CA2249472A1 (fr) 1997-10-02
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DE69705825D1 (de) 2001-08-30
AU2164497A (en) 1997-10-17
ATE203520T1 (de) 2001-08-15
ES2162268T3 (es) 2001-12-16
EP0888306B1 (de) 2001-07-25
JP3327925B2 (ja) 2002-09-24
US20020031536A1 (en) 2002-03-14
EP0888306A1 (de) 1999-01-07
FR2746391B1 (fr) 1998-04-17
FR2746391A1 (fr) 1997-09-26
US6322775B1 (en) 2001-11-27

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